Driven To Win

Chaz Wolfe
  • 5.0 (82)
  • Entrepreneurship
  • Updated Weekly

Driven To Win is the podcast for entrepreneurs who refuse to choose between building a successful business and building a strong family. Hosted by serial entrepreneur Chaz Wolfe, the show is built for business owners who want to scale their companies, lead stronger teams, and create a life that wins both at work and at home. Chaz built and scaled multiple businesses by his late twenties, becoming a millionaire by 29 and a multi-millionaire soon after through ventures in franchising, home services, real estate, and online education. His approach centers on leadership, systems, and structure that allow businesses to grow without the owner carrying all the weight. On Driven To Win, Chaz sits down with elite entrepreneurs, business leaders, authors, and operators to break down the real strategies behind growth. These are not surface level conversations. Each episode focuses on the practical disciplines required to build companies that run through strong leadership, clear structure, and effective sales systems. But business success is only half the conversation. Driven To Win is built around the belief that true success means winning in all areas of life. That includes business, family, health, faith, and lifestyle. Through honest conversations and practical insights, the show challenges entrepreneurs to build businesses that support their family life instead of competing with it. Listeners will learn how to: • Scale a business through leadership and systems • Develop stronger sales and operational discipline • Build teams that reduce owner dependence • Lead their family with the same intentionality they lead their company • Create a legacy that lasts beyond the business Whether you are building your first company or scaling an established business, Driven To Win delivers clear strategies and real conversations with leaders who are committed to growth in every area of life. If you are serious about building a business that creates freedom instead of pressure, this podcast is for you.

  1. 21h ago

    457 | After His Speech, This College Kid Asked Jim Rohn to Lunch. What Happened Next Changed Everything for Dan Rawitch

    Connect With Chaz Dan Rawitch started his career at nineteen years old by getting rejected from twelve interviews before someone finally gave him a shot. He went on to build the fourth largest mortgage credit reporting firm in the nation, trade bonds on Wall Street for Bear Stearns, and develop a trading indicator called Flight Station with an 87.5 percent win rate. Now he runs the University of Options with his daughters, teaching live trading classes and operating AI-powered trading bots that execute on his system automatically. In this conversation with Chaz Wolfe, Dan covers how he landed Jim Rohn as a mentor in college by simply taking his advice and asking him to lunch, why slow is fast when it comes to trading, how AI trading bots actually work and what makes them trustworthy or not, and why understanding money as energy is the mindset shift that unlocks everything else. Key Takeaways: Jim Rohn told a college audience that poor people should take rich people to lunch. Dan walked up after the speech and asked Jim to lunch. Jim said in all his years of giving that speech, no one had ever done that. Dan worked for him for nearly a year and learned more from him than from anyone else.Rohn told Dan to read for 30 minutes every night until he reached the highest pinnacle. He started with Think and Grow Rich and Psycho-Cybernetics, which led him to Silva Mind Control, which Dan says gave him a massive competitive advantage.For the first time in history, more options are traded than actual shares of stock. The learning curve is steep but short. Slow is fast. Paper trade first. Show your results before you trade real money.University of Options guarantees a 70 percent win rate or you do not pay. The system internally runs at an 87.5 percent win rate. Refunds are rare because failures are almost always about application, not the system.AI trading bots are built on years of data. The distinction that matters is between algorithm-based bots and neural networks that actually learn from their mistakes. Dan's bots do the latter.Every time Dan has hit a bottom in his career, he has catapulted. Tony Robbins says the bottom is a great springboard. You are not going to spring from the middle.Money is energy. Everything is built on energy and vibration. The people Dan has watched succeed were not always the most righteous people. They were the people 100 percent tuned in to what they wanted. That alignment is the real mechanism.Dan's dad lost the Cadillac, lost the big house, moved the family to a small town in Lancaster, and within three years was mayor, opened the first McDonald's, owned the biggest real estate firm, and owned the drive-in. He never seemed to care if he failed.You were put here to create. That is not a religious statement alone. It is a frequency alignment statement. When you stop waiting for permission and start creating, things come to you.Do not gear up your trading with your own capital until you are making enough to gear up with house money. The people who lose big are the ones who skipped the basics.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  2. 2d ago

    458 | He Lost $50K a Month in 5 Days. Armando LeDuc on the Client Journey System That Fixed Everything.

    Connect With Chaz Armando LeDuc lost close to $50,000 a month in retaining business in under five days. Clients were dropping. Bad reviews were coming in. Invoices were not getting paid. He was so confident in what he was doing that he had stopped actually paying attention to what his clients were experiencing. That humbling was the beginning of the client journey framework he now builds for businesses across the country. Armando is an actor, singer, filmmaker, entrepreneur, business coach, and the director of LeDuc Entertainment. His approach to personal branding is built on a simple premise: if you are going to sell it, you better be living it. When he started creating daily content for his own business the same way he told clients to, he hit $30,000 a month in revenue within the first month. In this conversation with Chaz Wolfe, Armando breaks down his three-step process for building a personal brand, how he mapped the complete client journey using the Domino's pizza tracker model and the five love languages, why he applies that same framework to referral partners and employees, and what happened when he finally stopped forcing his business forward and started living authentically. Key Takeaways: If you are going to sell it, you better be doing it. Most marketing companies tell clients to create content and build a brand while doing none of it themselves. That disconnect erodes trust before a conversation even starts.Daily content from the first month produced $30,000 in monthly revenue. Not because of reach. Because the preselling was done. By the time prospects got on a call, the question was not whether Armando could help them. It was whether they believed he could.Armando lost $50,000 in monthly retainers in under five days because there was no mapped client journey. Everybody goes on a journey whether you map it out or not. If you do not map it, the experience is inconsistent and eventually costs you.The Domino's pizza tracker model: clients know where they are in the process at all times. Who owns each touchpoint. What the KPIs are. What comes next. Clarity during fulfillment builds trust and eliminates invoice fights.The five love languages for clients: compliment their posts, leave them a Google review, refer them business, send a gift, or spend quality time with them. Armando built an automated pipeline that does all five on a rotating basis.The referral partner journey: most businesses only manage client obligations and completely ignore their referral partners. Armando built a separate pipeline for referral partners with the same love language touchpoints. Referrals went up significantly.The employee journey: the same intentionality that businesses apply to clients and referral partners should apply to the team. If you are treating everyone else like they matter and neglecting your own people, the team feels it.Planning heart touches is not inauthentic. Intentionality is the point. If you do not write it down, it will not happen. Preplanned giving is still giving.Living in shame is the lowest level of consciousness. Armando spent years dimming his energy because people around him could not handle it. The threshold he crossed at a mastermind conference was the moment he committed to stop wearing the mask.Authentic content attracts. Forced content repels. When you get clear on the one thing you are most passionate about and run all of your content through that lens, you stop guessing and start resonating.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTub Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  3. Sep 2

    459 | He Got Fired, Moved In With His Sister, and Started a Bonding Agency from $0. Neb Aynu's First Year.

    Connect With Chaz Neb Aynu was the top producer at his corporate bonding firm when he was let go. He had planned to start Kingdom Bonding in five years, at 35. Instead, he started it the same month. He moved in with his sister. He put his apartment on Airbnb. He put his car in a rental program. He walked places in the rain. His budget was under $100 a month. He worked 70 to 80 hours a week. In year one, Kingdom Bonding became one of the few minority-owned bonding-only agencies in the country. And Neb's contractors became something closer to family. In this conversation with Chaz Wolfe, Neb breaks down what bonding actually is and why it is the key to contractor success with government and large commercial contracts, how he built courage through David Goggins, forgiveness, and faith to turn the worst moment of his career into his biggest opportunity, and why he believes the real cause of America's wealth gap is not what most people think. Key Takeaways: Bonding is an insurance product for contractors doing work with federal, state, local, or general contractors. Without it, you cannot get the contract. Most contractors in the minority construction community do not know how to get bonded. That is the gap Neb is closing.Getting fired as the top producer taught Neb one thing: it was not about his work or his clients. It was about the box. Some people are not built for the box. Going all in on your own business becomes obvious when every other door closes.Neb prayed one prayer: close every single door so it is obvious I have to start Kingdom. God answered it. Every recruiter offered him insults. He incorporated May 13th.You cannot suppress pain as a man. You have to feel it, and then do something with it. Every time Neb felt bad, he worked harder. He channeled the frustration into the business until forgiveness replaced bitterness in November.Never Finished by David Goggins changed his headset from victim to victor. He listened to it the same month he incorporated. The timing was not a coincidence.Bitterness eats the person holding it. Forgiveness is not for the other person. It is for you. Neb had to go through a full forgiveness chapter to get his health and sanity back after the intensity of year one.The one decision that drove early success: give without expecting anything back. Neb creates weekly newsletters, weekly content, and weekly posts. He connects contractors who cannot benefit him personally. He educates the community for free. The relationships came back as clients and as brothers.The wealth gap is a mindset problem first and a knowledge gap second. Communities stuck in a scarcity mindset do not know what they do not know. Neb's mission is to teach minority contractors exactly how to get bonded, win federal contracts, and build real wealth, then watch them go back and teach the next person.Entrepreneurship is not an ethnicity thing. It is a mindset thing. But the stats show that the scarcity mindset is disproportionately concentrated in certain communities. Fixing that requires specific knowledge being delivered to specific people consistently.Serve people and connect them to each other, even when you get nothing out of it. Business is people to people to people. That is how growth happens.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  4. Aug 31

    460 | If You Build It, They Will Not Come. Rylee Meek on the Sales System Every Contractor Needs Right Now.

    Connect With Chaz Rylee Meek gave his life to entrepreneurship at fifteen. He started in network marketing, moved to personal training, discovered dinner seminar marketing at 26, made his first million dollar year selling insulation without knowing what the R value stood for, and has since built a nine-figure sales and client acquisition empire across industries including insurance, regenerative medicine, and home remodeling. He also co-founded The King's Council, a ministry and mastermind for faith-driven entrepreneurs. In this conversation with Chaz Wolfe, Rylee breaks down the dinner seminar model that changed his entire trajectory, why following your passion is the worst advice ever given, the predictable-sustainable-scalable selling system he builds into every business, and the seven-day creation template from Genesis that he now runs every business and life decision through. Key Takeaways: If you build it, they will not come. Unless you have a consistent, predictable flow of leads and sales, you do not have a business. You have a very expensive hobby.The number one enemy of every vision is lack of provision. You can have the greatest vision in the world, but if you cannot create enough value in the marketplace that someone will pay for, you have nothing.Do not follow your passion. Follow opportunity. But always bring your passion with you. Passion without opportunity is just a broke person with a great attitude.The dinner seminar breakthrough: delivering one presentation to 20 qualified prospects versus 20 individual presentations is leverage. Once Rylee discovered it in 2011 at age 26, he never went back. That year became his first million-dollar year.You cannot manage what you do not measure. If you do not know where in the funnel your leads are dropping off, you cannot fix it. Every advertising dollar is a seed. Know where it is landing.Build a predictable, sustainable, and scalable selling system. If you cannot dial it up or slow it down on command, you do not have a system. You have a hustle.Every product and service is a commodity unless you can articulate why a buyer should pay a premium for yours. If you cannot, you are competing on price. That is a race to the bottom.The seven-day Genesis blueprint applied to business: Day 1 is vision, Day 2 is culture and atmosphere, Day 3 is structure and playbook, Day 4 is order and implementation, Day 5 is momentum, Day 6 is dominion and fruitfulness, Day 7 is rest and reflection. Most entrepreneurs skip days 2 through 4 and wonder why the momentum fades.Rest is not weakness. The Sabbath was created for man. One day of rest and reflection allows you to pour gas on what is working and stop doing what is not. Entrepreneurs who never stop never know which is which.You were created to create. Whatever your faith background, the template of vision, atmosphere, structure, order, momentum, dominion, and rest is a framework that works in business and in life.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  5. Aug 26

    461 | It Is Not Your Customer's Job to Remember You. Clifton Muckenfuss on Why Most Contractor Businesses Lose Clients They Already Won.

    Connect With Chaz Clifton Muckenfuss co-founded a residential construction company in 2010 knowing nothing about construction. By the time he exited in 2021, 60 to 62 percent of his business was repeat and referral. He spent less than 1 percent of top-line revenue on direct response marketing. His Google reviews went from 3 in the first six years to over 100. None of that happened because of a marketing agency. It happened because Clifton built a system for expressing gratitude that turned satisfied clients into raving fans. In this conversation with Chaz Wolfe, Clifton breaks down the raving fan framework he now teaches business owners across the country, why a satisfied customer is actually a liability not an asset, the four-letter word that should alarm any contractor, and why the most expensive mistake most business owners make is stopping the relationship the moment the job is done. Clifton also shares the personal story behind why he built this in the first place. Multiple arrests. Aggravated assault charges. Drug sales and consumption. And a wife who looked him in the eye before the company existed and said: I don't know, but I believe in you. That one sentence changed everything. Key Takeaways: A raving fan is not just a happy customer. It is someone so obsessive about your people, your culture, your product, and your experience that they cannot wait to tell anyone who will listen.A satisfied customer is a liability. Fine is the four-letter word that should alarm you. Fine means something is wrong and they do not trust you enough to say what it is.It is not your customer's job to remember you. It is your job to make sure they cannot forget you. Most contractors complete the job and go find the next one. That is the gap.The biggest mistake most entrepreneurs make: they are too focused on the next opportunity and not focused enough on the key relationships that already exist. Your past customers know you, like you, and trust you. They are the easiest sale you will ever make.Clifton called a past client to thank them for a referral and casually asked about the windows. The client said do you do windows? Clifton had replaced their roof, deck, and siding. The client had no idea. That moment became the entire company philosophy.Referrals close at a higher rate. They buy at a higher price. They have fewer objections. And they lower your marketing costs. The gap between what you are currently spending on digital marketing and what you could spend by activating your existing relationships is almost entirely profit.Post-fulfillment follow-up is where most businesses fall apart. Right after a job is completed, when the client is at peak satisfaction, is the exact right moment to ask for a review, a video testimonial, and two or three referrals. Most business owners are too scared to ask because they are afraid something went wrong.If something went wrong, you want to know. A broken process that you cannot see cannot be fixed. The client who says fine and never calls again is more dangerous than the one who tells you exactly what went wrong.Express gratitude consistently and systematically. Relationship marketing is not a tactic. It is a philosophy that has to be built into every touch point before, during, and after the transaction.Internal raving fans matter just as much as external ones. Your employees and team members need to feel the same love and appreciation as your clients. The same gratitude framework applies to both.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  6. Aug 24

    462 | No Tenants. No Rehabs. No Rodents. Mark Podolsky on the Passive Income Model Nobody Talks About.

    Connect With Chaz Mark Podolsky spent years in investment banking with a 45-minute commute each way, buying things he did not care about to impress people who were not thinking about him. Then he started going to tax deed auctions on the side and buying raw undeveloped land for pennies on the dollar. He never looked back. Today Mark has done over 6,000 land deals, takes the entire month of July off every year to stress-test his team, travels globally at will, and runs what he calls a passive income machine built on three things: other people's time, software and automation, and other people's money. In this conversation with Chaz Wolfe, Mark walks through his entire land investing model step by step, explains why defaults are not actually a problem, why raw land is the most boring and least competitive niche in real estate, and why the only real mistake is stopping deal flow when you get scared. Key Takeaways: Raw land is an inefficient market. There is no MLS for dirt. Value is what a buyer and seller agree to. That inefficiency is the opportunity.Nobody wakes up thinking this is glamorous. That is the point. No HGTV show. No big money competition. No hedge funds. You and a million other investors could all be in this niche and run out of money before running out of deal flow.The model in one sequence: find a motivated seller with back taxes, offer 25 cents on the dollar of the lowest comparable sale, do due diligence for $11, buy it free and clear, sell it on terms to the neighbor or a buyer pool, collect a down payment and $297 a month for 72 months at 9 percent interest. No tenants. No rehabs. No renovations. No rodents.Defaults are not a disaster. They are a reset. The asset stays in your name under a land contract. You keep the down payment and all prior payments, lower your cost basis, and resell it. Sometimes defaults improve your ROI.The biggest mistake: fear-based decision making that stops deal flow. There is a 6-week lag between sending offers and getting responses. Stopping offers while you wait to sell inventory is how people stall the machine. In 20-plus years, Mark has never been stuck with a piece of land that would not sell at the right price.Entrepreneurs get bored with what works and go looking for the next county, the next niche, the next idea. The county that is making you money does not need to be replaced. It needs to be worked.Solo economic dependency is the trap. If you stop working, you stop making money. The land model solves that. $297 a month does not care whether you are at the office or in Bali.Freedom is not a number. It is a ratio. Mark's definition of enough: passive income at 200 percent of fixed expenses. Once you know your number, everything is just a game you choose to play.The happiest people have the best relationships. Money removes the biggest source of stress in a marriage and a family. It does not buy happiness. It buys the conditions for it.90 percent of the land business can be automated with inexpensive virtual assistants and software. The more automated the machine, the less valuable the owner needs to be to keep it running.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  7. Aug 17

    463 | The Five Financial Steps That Took Coach JV from Broke to a Rockefeller Trust for His Family

    Connect With Chaz In December 2006, John Vasquez attempted suicide. That is how he describes it. The person he was that day, a man drowning in opiate addiction and low self-worth, died. He considers it the beginning, not the end. Fourteen years later, the COVID pandemic shut down the gym he had built using Alex Hormozi's Gym Launch program, and he found himself sleeping on his parents' couch with two kids, back in the house he grew up in, watching his parents' same patterns around money and fear play out in real time. That was the moment he drew a line in the sand. Today Coach JV runs three seven-figure business ecosystems, has a Rockefeller Trust set up for his family for generations, and has built a massive social media following teaching financial literacy, micro and macroeconomics, and cryptocurrency education to people who were never taught any of it. In this conversation with Chaz Wolfe, Coach JV breaks down his 5-part financial framework, why Ray Dalio is the lens through which he reads the global economy, why paying yourself first is not just a strategy but a frequency shift, and how he is raising his kids to be the first generation to break the pattern for good. Key Takeaways: Drawing the line in the sand is not a motivational phrase. It is a moment when you become more committed to the pain of change than to the pain of staying the same. That specific shift is what changes the trajectory.You have to give up something to become something. And most people are addicted to their old self. The subconscious programming laid down in childhood drives adult behavior more than most people ever acknowledge.Coach JV's 5-part financial framework: Foundation, meaning rewire your belief system around money and trace where it came from. Financial Literacy, meaning understand what money actually is, how banks work, and what the Federal Reserve has done to the dollar since 1913. Discipline, meaning budgeting and asking do I need this or do I want this. Income Creation. And finally, Protection, Compounding, and Growth.The US dollar has collapsed 99 percent in purchasing power since the Federal Reserve was created in 1913. School, job, 401(k) is a strategy of hope. You are hoping the market aligns when you retire. That is not a plan.Pay yourself first every single time. Before bills. Before spending. Money goes into your freedom account first. What is left is what you live on. This changes your frame of mind and eliminates frivolous spending automatically.America is at 120 percent debt-to-income ratio. The average middle-class American needs to earn $160,000 per year to truly be middle class now. The regional banks are in a tough position. Bond yields inverted in 2023. These are not opinions. These are Ray Dalio's documented patterns.Cryptocurrency is going to move significantly on the back end of this cycle. But what goes up must come down hard. Buy the rumors, sell the news. When the mainstream is telling you to get in, you should have been out days ago.Define your principles before anything else. For Coach JV: business principles are integrity, honesty, and uncompromising belief in God. Personal principles are peace, freedom, and family structure. If anything disrupts those three, the answer is a hard no. A $10 million contract offer that disrupts family structure is still a no.Ask your son when he falls: are you hurt or are you scared? Manage what is hurt. Acknowledge the fear. Then get back up and do it again together. This is the framework Coach JV uses to rewire what he never received.Everything happening in the global economy right now is a historical pattern. It has happened before. When you understand the waves of energy, it is the greatest time in human history to build wealth for your family if you are paying attention.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

  8. Aug 12

    464 | Why Selling Your Business to a Holding Company Could Triple Your Exit. Josh Wilson Explains the Math.

    Connect With Chaz Josh Wilson started at seven years old on a cruise ship, charging his vacation friends a markup to use his grandfather's cruise card. He built a wedding DJ business at 16 and sold it at 19 for $25,000. His only W2 job was two months as a buggy boy at Winn Dixie before he got fired. Since then he has built a 25-million-dollar real estate portfolio, lost over a million dollars on a single investment, and pivoted to M&A where he is now acquiring his seventh company with a goal of 10 companies and 10 million in EBITDA before exiting to private equity. In this conversation with Chaz Wolfe, Josh breaks down the entire M&A framework he uses: what to look for in a target company, why he only buys companies doing at least a million in cashflow, the five reasons a contractor business owner should consider selling to a holding company instead of selling on the open market, why most businesses have not raised prices since COVID, and how the multiple arbitrage game works when you roll your equity into a holding company instead of taking a 3x exit alone. Key Takeaways: The first question in any acquisition: when was the last time they raised prices? Nine out of ten businesses Josh looks at have not raised prices in years. A 10 to 20 percent price increase is often the first value add after closing.Only buy companies doing at least one million in cashflow. Below that threshold, you cannot afford to hire the management team you need to actually run the business. You end up doing everything yourself again.A 3x multiple on your own is a mom-and-pop exit. Roll your equity into a holding company targeting 8 to 10x and you may triple your eventual payout for waiting a few years.PE companies buy cashflow, not hustle. When private equity looks at a portfolio, they want a C suite in place, a back office running, general managers in every entity, and systems that do not require the founder. Build that picture and you become attractive.Going wide to find your vertical is not always a mistake. Josh spent five years acquiring different industries to find where he could go deepest. He is now locking in on transportation. The path was the education.The mentor moment that changed everything: Josh was sitting in a hot tub during COVID, watching his real estate portfolio and wondering if his tenants were going to pay. In that moment he realized he could not keep living his entire life this way. That discomfort drove the pivot.If I can't do it, no one can is a guarantee that you will never scale. Josh learned it the hard way. The C suite he built is the only reason he can now focus exclusively on vision and growth.Pivoting is not failure. Real entrepreneurs master the art of knowing when things are heading in the wrong direction and correcting course before it costs them everything.$25,000 was enough to count as a real exit. The size of the deal does not determine whether the principle applied. Josh knew how to create value and find a buyer at 19 years old. The same principle runs his 7-company portfolio today.Build the right C suite first. CFO, COO, CEO roles need to be filled by people who love operating, not just people who are available. Josh found each one through deliberate relationships, not desperation.If you are a contractor business owner doing $1M+ and you feel stuck in the day-to-day, we built GTK for you. Through peer mastermind and 1:1 coaching, we help you: increase profitinstall real systemsbuild a team that runs the businessget your time backVisit www.gatheringthekings.com for information on how to apply. Connect with Chaz Wolfe (Host): Website Facebook Instagram LinkedIn YouTube Profit Starts with Better Books!Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show Like what you heard? Share this episode with a friend and leave us a review on Apple Podcasts or Spotify! Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

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82 Ratings

About

Driven To Win is the podcast for entrepreneurs who refuse to choose between building a successful business and building a strong family. Hosted by serial entrepreneur Chaz Wolfe, the show is built for business owners who want to scale their companies, lead stronger teams, and create a life that wins both at work and at home. Chaz built and scaled multiple businesses by his late twenties, becoming a millionaire by 29 and a multi-millionaire soon after through ventures in franchising, home services, real estate, and online education. His approach centers on leadership, systems, and structure that allow businesses to grow without the owner carrying all the weight. On Driven To Win, Chaz sits down with elite entrepreneurs, business leaders, authors, and operators to break down the real strategies behind growth. These are not surface level conversations. Each episode focuses on the practical disciplines required to build companies that run through strong leadership, clear structure, and effective sales systems. But business success is only half the conversation. Driven To Win is built around the belief that true success means winning in all areas of life. That includes business, family, health, faith, and lifestyle. Through honest conversations and practical insights, the show challenges entrepreneurs to build businesses that support their family life instead of competing with it. Listeners will learn how to: • Scale a business through leadership and systems • Develop stronger sales and operational discipline • Build teams that reduce owner dependence • Lead their family with the same intentionality they lead their company • Create a legacy that lasts beyond the business Whether you are building your first company or scaling an established business, Driven To Win delivers clear strategies and real conversations with leaders who are committed to growth in every area of life. If you are serious about building a business that creates freedom instead of pressure, this podcast is for you.

Information

  • Creator
    Chaz Wolfe
  • Years Active
    2022 - 2026
  • Episodes
    60
  • Rating
    Explicit
  • Copyright
    © 2026 485188
  • Show Website
    Driven To Win

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